42858-39-9

Basic information

• Product Name: ETHYL BICYCLO[2.2.2]OCT-5-ENE-2-CARBOXYLATE
• Synonyms: ETHYL BICYCLO[2.2.2]OCT-5-ENE-2-CARBOXYLATE;Ethyl bicyclo[2.2.2]oct-5-ene-2-carboxylate, 95+%;ETHYL BICYCLO(2,2,2)OCT-2-EN-5-CARBOXYLATE (MIX OF ENDO + EXO)
• CAS NO: 42858-39-9
• Molecular Formula: C₁₁H₁₆O₂
• Molecular Weight: 180.24
• Mol File: 42858-39-9.mol

Chemical Properties

• Boiling Point: 237.9°Cat760mmHg
• Flash Point: 88.9°C
• Appearance: /
• Density: 1.057g/cm³
• Vapor Pressure: 0.0437mmHg at 25°C
• Refractive Index: 1.5
• CAS DataBase Reference: ETHYL BICYCLO[2.2.2]OCT-5-ENE-2-CARBOXYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: ETHYL BICYCLO[2.2.2]OCT-5-ENE-2-CARBOXYLATE(42858-39-9)
• EPA Substance Registry System: ETHYL BICYCLO[2.2.2]OCT-5-ENE-2-CARBOXYLATE(42858-39-9)

Safety Data

• Hazardous Substances Data: 42858-39-9(Hazardous Substances Data)

Usage

Uses

Used in Fragrance Industry:
ETHYL BICYCLO[2.2.2]OCT-5-ENE-2-CARBOXYLATE is used as a fragrance ingredient for its pleasant odor, enhancing the scent profiles of various products.
Used in Flavoring Industry:
In the flavoring industry, ETHYL BICYCLO[2.2.2]OCT-5-ENE-2-CARBOXYLATE is used as a flavoring agent to impart or modify taste in food and beverage products.
Used in Pharmaceutical Industry:
ETHYL BICYCLO[2.2.2]OCT-5-ENE-2-CARBOXYLATE is used as an active pharmaceutical ingredient or as an excipient in the development and formulation of medications due to its potential biological activity.
Used as a Solvent:
ETHYL BICYCLO[2.2.2]OCT-5-ENE-2-CARBOXYLATE is utilized as a solvent in various chemical processes, providing a medium for reactions to occur.
Used as a Chemical Intermediate:
In the chemical industry, ETHYL BICYCLO[2.2.2]OCT-5-ENE-2-CARBOXYLATE serves as an intermediate in the synthesis of other chemicals, contributing to the production of a range of compounds.
ETHYL BICYCLO[2.2.2]OCT-5-ENE-2-CARBOXYLATE is considered to have low toxicity and is relatively safe for use across these applications.

InChI:InChI=1/C11H16O2/c1-2-13-11(12)10-7-8-3-5-9(10)6-4-8/h3,5,8-10H,2,4,6-7H2,1H3

Upstream product

• 42216-96-6 triethyl orthoacrylate 
• 1165952-91-9 cyclohexa-1,3-diene 
• 140-88-5 ethyl acrylate 

Downstream Products

• 39863-21-3 2-Carboethoxy<2.2.2>bicyclooctadien-2.5 
• 60774-54-1 2-(Phenylthio)-bicyclo-<2.2.2>-oct-5-en-2-carbonsaeureethylester 
• 60774-70-1 2-(Phenylsulfinyl)-bicyclo<2.2.2>-oct-5-en-2-carbonsaeureethylester 
• 20507-56-6 (2-endo)-bicyclo<2.2.2>oct-5-ene-2-carboxylic acid 

Relevant articles and documents

ON THE REVERSIBILITY OF ALKENE CYCLOZIRCONATION

Diene 8, under cyclozirconation conditions, rapidly dimerizes to 10.This dimerization is reversible, slowly at room temperture and rapidly at 75 deg C.After equilibration, the dominant product is 12, the product of intramolecular cyclozirconation. Key words: carbocyclization, cyclometallation, cyclozirconation, diastereoselective, reversible, equilibrating

Synthesis and computational analysis of conformationally restricted [3.2.2]- and [3.2.1]-3-azabicyclic diamines

Conformational restriction is a useful approach for ligand design in organic and medicinal chemistry. This manuscript reports the facile synthesis and in silico conformational analysis of two new diastereomeric [3.2.2]-3-azabicyclic, two new [3.2.1]-3-aza-8-oxy-bicyclic and one new [3.2.1]-3-azabicyclic diamine scaffolds. A conformational analysis of these structures along with calculation of carbon–carbon/carbon–nitrogen bond angles was carried out and compared to those in the flexible 1,3-diaminopropane template upon which they were based. It is of particular importance that these scaffolds have bond lengths and angles that can overlap with low energy conformers of the flexible diamine. Such information is useful for ligand design in organic chemistry and for development of structure activity relationships and in silico screening in medicinal chemistry.

Synthesis and in vitro platelet aggregation and TP receptor binding studies on bicyclic 5,8-ethanooctahydroisoquinolines and 5,8-ethanotetrahydroisoquinolines

Eighteen novel bicyclic 1-substituted benzyl octahydro- and tetrahydroisoquinolines were synthesized and evaluated for human thromboxane A2/prostaglandin H2 (TP) receptor affinity and antagonism of TP receptor-mediated platelet aggre

Catalysis by organic solids. Stereoselective Diels-Alder reactions promoted by microporous molecular crystals having an extensive hydrogen- bonded network

Anthracenebisresorcinol derivative 1 as an organic network material shows a novel catalysis in the solid state for the acrolein-cyclohexadiene Diels-Alder reaction. The suggested mechanism involves a catalytic cycle composed of sorption of the reactants in the cavities of polycrystalline host 1, preorganized intracavity reaction, and desorption of the product. The host also promotes stereoselective intracavity reactions for alkyl acrylates and cyclohexadiene but, in this case, not in a catalytic manner. Relevance of the present system as a functional organic analog of zeolites is discussed in light of the kinetics of respective elementary processes and the effects of pulverization of the catalyst thereupon as well as X-ray crystal structures.

The Low-Temperature, Ionic Diels-Alder Addition of Vinyl Ortho Esters to 1,3-Dienes

3,3,3-Triethoxypropene (triethyl orthoacrylate) was added to a series of 1,3-dienes in the presence of trimethylsilyl triflate at -78 to 0 deg C to produce 53-83percent yields of the adduct of ethyl acrylate and the 1,3-dienes.The products were formed und

DEAMINATION OF BICYCLOOCTAN-2-YL- AND BICYCLOOCTAN-2-YL-AMINES. EVIDENCE FOR CLASSICAL PRECURSORS OF NON-CLASSICAL CARBONIUM IONS

Bicyclo octan-2-yl- and exo-bicyclooctan-2-yl-amines have been deaminated in acetic acid by nitrous acid and via their N-phenyltriazenes; their ethyl N-nitrosocarbamates have also been solvolysed in ethanol.Product distributions by a given method from the structurally isomeric starting materials are similar to each other and to common product distribution obtained from bicyclooctan-2-yl and exo-bicyclooctan-2-yl toluene-p-sulphonates.Each amine gives, however, a small but unmistakable excess of the structurally unrearranged product compared (in the case of subtitution) with the distribution obtained from the solvolysis of the corresponding bicyclo-octyl toluene-p-sulphonates. endo-Bicyclooctan-2-ylamine has also been deaminated in acetic acid by nitrous acid and via its ethyl N-nitrosocarbamate in ethanol.The prouct ratios of these reactions are characteristically different from those of the isomric amines but, as far as substitution is concerned, are similar to what is obtained from endo-bicyclooctan-2-yl toluene -p-sulphonate.A common mechanism describes all the deaminative reactions.We propose that classical carbonium ions are the initial products of fragmentation of diazo-intermediates.These are intercepted to only a small extent to give products structurally and stereochemically characteristic of the original amines; to an even smaller extent they rearrange to isomeric classical carbonium ions, which in turn may be intercepted.The predominant reaction of the initially formed classical carbonium ions is rearrangement to non-classical isomers.From both becyclooctan-2-yl- and exo-bicyclooctan-2-yl-amines, the same unsymmetrical nonclassical carbonium ion is produced as has been implicated in the solvolysis of the corresponding toluene-p-sulphonates. endo-Bicyclooctan-2-ylamine deamination gives rise to an isomeric symmetrical non-classical carbonium ion, the same one that intervenes in the solvolysis of endo-bicyclo-octan-2-yl toluene-p-sulphonate.Symmetrical and unsymmetrical non-classical carbonium ions once formed give product ratios largely independent of their origins or modes of formation although the symmetrical one appears to undergo a small extent of isomerization to the (more stable) unsymmetrical species.These results are contrasted with those obtained from simple carbocyclic systems (without branching at the β-carbon) in which deamination and toluene-p-sulphonate solvolysis give characteristically different and unrelated product distributions.